My first time was in 1980, I was 17. Visited a Private Shop (older UK guys will remember these, an adult bookstore chain) around 8pm. Obviously gay fella working there, mid 20s.
I asked about contact mags (if you remember such things), he asked if I was looking for lesbians, I said anything really. He started playing with his zipper and said he could lock the door if I wanted some fun.
I said yes.
He locked the door and unzipped, a nice uncut cock, decent size. Wanted me to suck him but I hadn't done it before so just wanked him a bit.
He got me out of my jeans and asked if I wanted him to fuck me. Told him I was a virgin. He looked surprised, asked me if I really was. Said yes. He said he knew a guy who was generous with cherry boys. He mentioned a figure that was very attractive, so I said why not?
Waited for him to lock up the shop and he drove me to a big house not very far away, him feeling my hard-on all the time in the car.
Arrived and knocked on the door, older guy answered, def in his 60s, looked at me and smiled. I went in and shop guy left.
Old guy asked if I was a virgin, I said yes. He asked did I want to lose my cherry, said he'd be generous. I said OK.
He led me upstairs and into the bathroom, had me strip and bend over, gave my tight hole a quick inspection, then took me into the bedroom.
Another old guy in the bedroom, on the bed, naked, wanking. 1st guy said if I wanted the cash I'd have to have them both, but it was a good sum so said yes.
Next thing I was face down on the bed, arms held and a pillow under me, ass in the air and being lubed up. 1st guy enters me, hurt like fuck, humped for a while and shot his load in me (pre AIDS). I was crying. They swapped and the 2nd guy flipped me over, lifted my legs and fucked by spunky hole with me on my back. He was bigger and it hurt even more. He also spunked in me.
They both did me at least twice more until my ass was bleeding.